Aqueous solutions of addition com



Patented June 9, 1936 UNITED STATES PATENT OFFICE 2,043,650 AQUEOUS SOLUTIONS OF ADDIT ON oOM- POUNDS OF ALKYLACRIDINIUM SALTS WITH HEAVY METAL SALTS AND A PROC- ESS F PREPARING THEM No Drawing.

Application March 28, 1935, Serial No. 13,580. In Germany May 26, 1932 13 Claims. (Cl. 260-11) v for instance, been described in our co-pending The present invention relates to aqueous solutions of addition compounds of alkylacridinium salts with heavy metal salts and to a process of preparing them.

In our co-pending application Serial No. 13,579 filed March 28, 1935 there is described a process for preparing salts of acridinium bases by transforming salts of the ammonium bases into the bicarbonates and then dissolving the latter in any acids.

Now we have found that aqueous solutions of valuable complex heavy metal addition compounds of acridinium bases are obtained by mixing with heavy metal salts the water-soluble salts of acridinium bases obtainable, for instance, according to the above named application. This process allows the combined pharmaceutical application of quaternary ammonium salts with heavy metal salts, for instance, silver salts. Whereas, as is known, the chlorides and sulfates of the quaternary ammonium bases cannot be applied simultaneously with silver salts on account of the formation of insoluble silver salts, complex silver compounds of the ammonium salts may readily be obtained with the aid of the bicarbonates. In this case the bicarbonates are dissolved in an organic acid, such as lactic acid, and when the evolution of carbon dioxide gas has ceased silver lactate is added, completely stable solutions of the silver ammonium salts being thus obtained.

The following table shows the results of tests regarding the solubilities of some of the acridinium salts obtainable by Way of the bicarbonates, and of their heavy metal compounds; the limit of solubility was not attained in these tests:

3,6-diamino--methylacridinium acetate 3,6-diamin0-l0-methylacridinium glycolate--. 3,6-diamino-IO-methylacridinium aminoacetat 3,6diaminO-IO-methyIacridinium citrate The quinic acid salt of 3,6-diamino-l0-methylacr ium base- 3,6-diamino l0-methylacridinium-alpl1a-hydroxyphenylacetate 3,fi-diamino-lO-acridinium lactate 3,ii-iiamino-lO-methylacridinium lactate copper acea e- 3,6-diamino-lO-methylacridinium lactate lead acetate at least 1:10

3,G-diamino-lO-methylacridinium acetate copper acetate application above referred to. Carboxylic acids, in which the bicarbonates may be dissolved are, for instance, formic acid, acetic acid, propionic acid, butyric acid, lactic acid, tartaric acid, benzoic acid, ortho-toluic acid, meta-toluio acid, para-toluic acid, glycollic acid, citric acid, gluconic acid, and quinic acid. As heavy metal salts there may be'used the saltsof the above named acids with copper, silver, gold, iron, mercury, lead, particularly those of the first group of the periodic system, for instance, silver lactate, silver acetate, cupric acetate, lead acetate, mercuric acetate and ferric acetate.

The following example serves to illustrate the invention, but it is not intended to limit it thereto 2.2 grams of the bicarbonate of 3.6-diamino-10- methylacridinium hydroxide prepared, for instance, according to Example 1 of our co-pending application above referred to, are mixed with 0.9 gram of lactic acid of 90 per cent strength; the whole is made up to 200 cc. after addition of 1.5 grams of silver lactate. The solution is stable. If desired, buffer substances may be added or the solution may be adjusted to neutral reaction.

We claim:

1. The process which comprises dissolving the bicarbonate of an acridinium base substituted at the nitrogen by an alkyl radical of the lower series in a carboxylic acid forming a water-soluble salt with said base and causing a water-soluble heavy metal salt of carboxylic acid to act in the presence of water upon the water-soluble alkylacridinium salt thus obtained.

2. The process which comprises dissolving the bicarbonate of an acridinium base substituted at the nitrogen by an alkyl radical of the lower series in a lower aliphatic carboxylic acid forming a water-soluble salt with said base and causing a water-soluble heavy metal salt of carboxylic acid to act in the presence of water upon the water-soluble alkylacridinium salt thus obtained.

3. The process which comprises dissolving the bicarbonate of a methylacridinium base in a lower aliphatic carboXylic acid forming a watersoluble salt with said base and causing a watersoluble salt of a heavy metal from the first group of the periodic system and a carboxylic acid to act in the presence of water upon the watersoluble methylacridinium salt thus obtained.

4. The process which comprises dissolving 3.6- diamino-l0-methylacridinium bicarbonate in lactic acid and causing silver lactate to act in the presence of water upon the acridinium lactate thus obtained.

5. The process which comprises causing a water-soluble salt or" an acridinium base substituted at the nitrogen by an alkyl radical of the lower series with a carboxylic acid to act upon a water-soluble heavy metal salt of a carboxylic acid in the presence of water.

6; The process which comprises causing a water-soluble salt of an acridinium base substituted at the nitrogen by an alkyl radical of the lower series with a lower aliphatic carboxylic acid to act upon a water-soluble heavy metal salt of a carboxylic acid in the presence of water.

7. The process which comprises causing a water-soluble salt of a methylacridinium base with a lower aliphatic carboxylic acid to act in the presence of water upon a water-soluble salt of a heavy metal from the first group of the periodic system and a carboxylic acid.

8. The process which comprises causing the lactate of 3,6-diarm'no-IO-methylacridinium hydroxide to act upon silver lactate in the presence of water.

9. Aqueous solutions of complex addition compounds of water-soluble salts of acridinium bases substituted at the nitrogen by an alkyl radical of the lower series with water-soluble salts of heavy metals of carboxylic acids, said solutions showing valuable therapeutic properties.

10. Aqueous solutions of complex addition compounds of water-soluble carboxylic acid salts of acridinium bases substituted at the nitrogen by an alkyl radical of the lower series with watersoluble salts of heavy metals of carboxylic acids, said solutions showing valuable therapeutic properties.

11. Aqueous solutions of complex addition compounds of water-soluble lower aliphatic oarboxylic acid salts of acridinium bases substituted at the nitrogen by an alkyl radical of the lower series with water-soluble salts of heavy metals of carboXylic acids, said solutions showing valuable therapeutic properties.

12. Aqueous solutions of complex addition compounds of Water-soluble lower aliphatic carboxylic acid salts of methyl-acridinium bases with water-soluble salts of heavy metals from the first group of the periodic system and carboxylic acids, said solutions showing valuable therapeutic properties.

13. Aqueous solutions of the complex addition compounds of 3.6-diamino-IO-methylacridinium lactate with silver lactate, said solutions showing valuable therapeutic properties.

MAX BocKMiiHL. LEONHARD STEIN. 

